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I have the new iMac (Sept 2017) and my iTunes Library transferred correctly, but some playlists won't shuffle. Hitting the shuffle (upper right) does nothing. Other playlist shuffle with no problems. I checked the repeat function and it is off. I transferred the songs to a new playlist, but the new playlist won't shuffle either.
Look forward to your suggestions.
Thanks - Hank
iMac (Retina 5K, 27-inch, 2017), iOS 11.2, Operating High Sierra
Check to make sure that you don't have the "skip when shuffling" check box selected. I forget this every year at christmas time since I don't want those songs playing the rest of the year...
iTunes Shuffle won't work on some playlists
